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Photophysics and Photochemistry of Sterically Strained α-Halo-Anthraquinones: the Bromo and/or Chloro Substituted Compounds

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The steric hindrance between the oxygen and halogen atoms results in the structural deformation of α-haloanthraquinones and their lowest excited triplet (T1) states are of mixed nπ*-ππ* or ππ* character with unusually short lifetimes. Moreover, the rates of hydrogen-atom abstraction from ethanol by the T, states decrease with their increasing ππ* character, and the proximity of the halogen atom to the hydroxy group causes the photochemical intramolecular elimination of hydrogen halide from the initial photoproducts (α-haloanthrahydroquinones) yielding α-haloanthraquinones (or anthraquinone) with one less halogen atom than the original molecule; the final product is anthrahydroquinone. The remarkably large structural deformation of 1,8-dihaloanthraquinones, furthermore, makes it possible to observe an absorption band due to a complex of two 1,8-dihaloanthrasemiquinone radicals which gives rise to the simultaneous formation of 1,8-dihaloanthrahydroquinones and the original anthraquinones. Of particular interest is observation of the absorption band(s) attributable to the second excited triplet (T2) states of 1,8-dihaloanthraquinones. However, the electron transfer from triethylamine (TEA) to these T2 states generating the radical anions is observed only in acetonitrile, while that to the T1 states generating their exciplexes with TEA is observed not only in acetonitrile but also in toluene and ethanol.

Affiliations: 1: Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606, Japan


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